Identification

Name
Memantine
Accession Number
DB01043  (APRD00221)
Type
Small Molecule
Groups
Approved, Investigational
Description

Memantine is an amantadine derivative with low to moderate-affinity for NMDA receptors. It is a noncompetitive NMDA receptor antagonist that binds preferentially to NMDA receptor-operated cation channels. It blocks the effects of excessive levels of glutamate that may lead to neuronal dysfunction. It is under investigation for the treatment of Alzheimer's disease, but there has been no clinical support for the prevention or slowing of disease progression.

Structure
Thumb
Synonyms
  • 1-Amino-3,5-dimethyladamantane
  • 1,3-Dimethyl-5-adamantanamine
  • 3,5-Dimethyl-1-adamantanamine
  • 3,5-Dimethyl-1-aminoadamantane
  • 3,5-Dimethyltricyclo(3.3.1.1(3,7))decan-1-amine
  • Memantina
  • Memantine
  • Memantinum
External IDs
D-145 / DRG-0267
Product Ingredients
IngredientUNIICASInChI Key
Memantine HydrochlorideJY0WD0UA6041100-52-1LDDHMLJTFXJGPI-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act MemantineTablet5 mgOralActavis Pharma CompanyNot applicableNot applicableCanada
Act MemantineTablet10 mgOralActavis Pharma Company2010-02-18Not applicableCanada
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated20 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
AxuraTablet, film coated10 mgOralMerz Pharmaceuticals2002-05-17Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-memantineTablet10 mgOralApotex Corporation2011-06-17Not applicableCanada
MarixinoTablet, film coated20 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated20 mgOralKrka, D.D.2013-04-29Not applicableEu
MarixinoTablet, film coated10 mgOralKrka, D.D.2013-04-29Not applicableEu
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Memantine and Donepezil Hydrochlorides Extended-releaseMemantine Hydrochloride (14 mg/1) + Donepezil hydrochloride (10 mg/1)Capsule, extended releaseOralAmneal Pharmaceuticals2017-02-01Not applicableUs
Memantine and Donepezil Hydrochlorides Extended-releaseMemantine Hydrochloride (28 mg/1) + Donepezil hydrochloride (10 mg/1)Capsule, extended releaseOralAmneal Pharmaceuticals2017-02-01Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitVivimed Labs Limited2015-09-04Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitOralActavis Pharma Company2015-04-01Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitWockhardt2015-09-04Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitVivimed Labs Limited2015-09-04Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitOralActavis Pharma Company2015-04-01Not applicableUs
Memantine HydrochlorideMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitWockhardt2015-09-04Not applicableUs
NamendaMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitOralAllergan, Inc.2003-10-16Not applicableUs
NamendaMemantine Hydrochloride (5 mg/1) + Memantine Hydrochloride (10 mg/1)KitOralAllergan, Inc.2003-10-16Not applicableUs
International/Other Brands
Abixa / Akatinol / Axura / Memox
Categories
UNII
W8O17SJF3T
CAS number
19982-08-2
Weight
Average: 179.3018
Monoisotopic: 179.167399677
Chemical Formula
C12H21N
InChI Key
BUGYDGFZZOZRHP-UHFFFAOYSA-N
InChI
InChI=1S/C12H21N/c1-10-3-9-4-11(2,6-10)8-12(13,5-9)7-10/h9H,3-8,13H2,1-2H3
IUPAC Name
3,5-dimethyladamantan-1-amine
SMILES
CC12CC3CC(C)(C1)CC(N)(C3)C2

Pharmacology

Indication

For the treatment of moderate to severe dementia of the Alzheimer's type.

Associated Conditions
Pharmacodynamics

Memantine, an amantadine derivative, is an NMDA receptor antagonist used in the treatment of Alzheimer's disease. It differs from traditional agents used in Alzheimer's disease by acting on glutamatergic neurotransmission, rather than cholinergic. There is some evidence that dysfunction of glutamatergic neurotransmission, manifested as neuronal excitotoxicity, is involved in the aetiology of Alzheimer's disease (Cacabelos et al., 1999). As such, targeting the glutamatergic system, specifically NMDA receptors, was a novel approach to treatment in view of the limited efficacy of existing drugs targeting the cholinergic system. A systematic review of randomised controlled trials found that memantine has a positive effect on cognition, mood, behaviour, and the ability to perform daily activities. There is no evidence that memantine prevents or slows neurodegeneration in patients with Alzheimer's disease.

Mechanism of action

Memantine exerts its action through uncompetitive NMDA receptor antagonism, binding preferentially to the NMDA receptor-operated cation channels. Prolonged increased levels of glutamate in the brain of demented patients are sufficient to counter the voltage-dependent block of NMDA receptors by Mg2+ ions and allow continuous influx of Ca2+ ions into cells, ultimately resulting in neuronal degeneration. Studies suggest that memantine binds more effectively than Mg2+ ions at the NMDA receptor, and thereby effectively blocks this prolonged influx of Ca2+ ions through the NMDA channel whilst preserving the transient physiological activation of the channels by higher concentrations of synaptically released glutamate. Thus memantine protects against chronically elevated concentrations of glutamate. Memantine also has antagonistic activity at the type 3 serotonergic (5-HT3) receptor with a potency that is similar to that at the NMDA receptor, and lower antagonistic activity at the nicotinic acetylcholine receptor. This drug has no affinity for γ-aminobutyric acid (GABA), benzodiazepine, dopamine, adrenergic, histamine, or glycine receptors or for voltage-dependent calcium, sodium, or potassium channels.

TargetActionsOrganism
AGlutamate receptor ionotropic, NMDA 3A
antagonist
Human
AGlutamate receptor ionotropic, NMDA 2A
antagonist
Human
AGlutamate receptor ionotropic, NMDA 2B
antagonist
Human
U5-hydroxytryptamine receptor 3A
antagonist
Human
UAlpha-7 nicotinic cholinergic receptor subunit
antagonist
Human
UD(2) dopamine receptor
agonist
Human
UGlutamate receptor ionotropic, NMDA 1
binder
Human
Absorption

Well absorbed orally with a bioavailability of approximately 100%. Peak plasma concentrations are reached in 3-7 hours. Food has no effect on absorption.

Volume of distribution
  • 9 to 11 L/kg
Protein binding

45%

Metabolism

Excreted largely unchanged. About 20% is metabolized to 1-amino-3-hydroxymethyl-5-methyl-adamantane and 3-amino-1-hydroxy-5,7-dimethyl-adamantane.

Route of elimination

Memantine undergoes partial hepatic metabolism. About 48% of administered drug is excreted unchanged in urine; the remainder is converted primarily to three polar metabolites which possess minimal NMDA receptor antagonistic activity: the N-glucuronide conjugate, 6-hydroxy memantine, and 1-nitroso-deaminated memantine. It is excreted predominantly in the urine, unchanged.

Half life

60-100 hours

Clearance
Not Available
Toxicity

Side effects include pain, abnormal crying, leg pain, fever, increased apetite. Adverse drug reactions include: dizziness, confusion, headache, hallucinations, tiredness. Less common side effects include: vomiting, anxiety, hypertonia, cystitis, and increased libido. Doses of up to 400 mg have been tolerated.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Memantine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Memantine.
AbacavirMemantine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Memantine which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Memantine which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Memantine which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Memantine.
AcetaminophenAcetaminophen may decrease the excretion rate of Memantine which could result in a higher serum level.
AcetazolamideThe excretion of Memantine can be decreased when combined with Acetazolamide.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Memantine which could result in a higher serum level.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
US3391142
General References
  1. Cacabelos R, Takeda M, Winblad B: The glutamatergic system and neurodegeneration in dementia: preventive strategies in Alzheimer's disease. Int J Geriatr Psychiatry. 1999 Jan;14(1):3-47. [PubMed:10029935]
  2. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
  3. Robinson DM, Keating GM: Memantine: a review of its use in Alzheimer's disease. Drugs. 2006;66(11):1515-34. [PubMed:16906789]
  4. Rogawski MA: Low affinity channel blocking (uncompetitive) NMDA receptor antagonists as therapeutic agents--toward an understanding of their favorable tolerability. Amino Acids. 2000;19(1):133-49. [PubMed:11026482]
  5. Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [PubMed:11403963]
External Links
Human Metabolome Database
HMDB0015177
KEGG Compound
C13736
PubChem Compound
4054
PubChem Substance
46506702
ChemSpider
3914
BindingDB
50062599
ChEBI
64312
ChEMBL
CHEMBL807
Therapeutic Targets Database
DAP000493
PharmGKB
PA10364
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Memantine
ATC Codes
N06DX01 — MemantineN06DA52 — Donepezil and memantineN06DA53 — Donepezil, memantine and ginkgo folium
AHFS Codes
  • 28:92.00 — Miscellaneous Central Nervous System Agents
FDA label
Download (102 KB)
MSDS
Download (65.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherAutism Spectrum Conditions/Disorders1
0RecruitingTreatmentStroke, Ischemic / Upper Extremity Weakness1
1Active Not RecruitingTreatmentBrain Cancer1
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableHealthy Volunteers / Obese, Otherwise Healthy Volunteers1
1CompletedBasic ScienceBioequivalence, AUC, Cmax, Pharmacokinetics1
1CompletedBasic ScienceMajor Depressive Disorder (MDD)1
1CompletedTreatmentTobacco Use Disorders2
1RecruitingTreatmentAlzheimer's Disease (AD) / Battery1
1RecruitingTreatmentHealthy Volunteers1
1WithdrawnTreatmentAlzheimer's Disease (AD)1
1, 2Active Not RecruitingTreatmentChronic Orthostatic Intolerance / Tachycardia1
1, 2RecruitingHealth Services ResearchSchizophrenic Disorders1
1, 2RecruitingTreatmentStimulants Use Disorder1
2CompletedOtherAlcohol Drinking2
2CompletedSupportive CareCancer, Breast / Colorectal Cancers / Lung Cancers / Prostate Cancer / Tobacco Use Disorders1
2CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAlcohol Abuse / Alcohol Dependence (Primary Condition)1
2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)2
2CompletedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Child Development Disorder / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2CompletedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2CompletedTreatmentAutism Spectrum Conditions/Disorders1
2CompletedTreatmentAutism, Early Infantile1
2CompletedTreatmentAutism, Early Infantile / Pediatric Autism1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentCompulsive Buying1
2CompletedTreatmentDementia Associated With Parkinson's Disease / Diffuse Lewy Body Disease1
2CompletedTreatmentDementias1
2CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentHuntington's Disease (HD)1
2CompletedTreatmentKleptomania1
2CompletedTreatmentMemory Disorders / Memory, Concentration or Attention Problems / Retention Disorders, Cognitive / Subjective Cognitive Impairment1
2CompletedTreatmentObsessive Compulsive Disorder (OCD)1
2CompletedTreatmentOpioid Dependence1
2CompletedTreatmentPain, Neuropathic1
2CompletedTreatmentPathological Gambling1
2CompletedTreatmentPendular Nystagmus Patients With Multiple Sclerosis1
2CompletedTreatmentSchizophrenic Disorders1
2Not Yet RecruitingTreatmentPain, Neuropathic1
2Not Yet RecruitingTreatmentSickle Cell Disorders1
2RecruitingSupportive CareEpendymomas / Germ Cell Tumors / Glioma of Brain / Postsurgical craniopharyngioma1
2RecruitingTreatmentAmyotrophic Lateral Sclerosis (ALS) / Frontal Temporal Dementia (FTD)1
2RecruitingTreatmentBipolar Disorder (BD)1
2RecruitingTreatmentDisability, Intellectual / Down Syndrome (DS)1
2RecruitingTreatmentLupus Erythematosus, Systemic1
2TerminatedTreatmentAsperger's / Asperger's Disorder / Autism Spectrum Conditions/Disorders / Autism, Early Infantile / Autistic Disorder / Pediatric Autism / Pervasive Developmental Disorder Not Otherwise Specified (PDD-NOS)1
2TerminatedTreatmentDisseminated Sclerosis1
2TerminatedTreatmentGlioblastomas1
2TerminatedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2, 3CompletedTreatmentAlzheimer's Disease (AD) / Major Depressive Disorder (MDD) / Mild Cognitive Impairment (MCI)1
2, 3CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2, 3CompletedTreatmentBipolar Disorder (BD)1
2, 3CompletedTreatmentHeroin Dependence / Opioid Dependence1
2, 3CompletedTreatmentOpioid Dependence1
2, 3RecruitingTreatmentCognitive Impairments1
2, 3Unknown StatusTreatmentCognition Disorders / Disseminated Sclerosis1
3Active Not RecruitingSupportive CareCognitive Impairments / Metastatic Malignant Neoplasm in the Brain / Solid Neoplasms1
3Active Not RecruitingSupportive CareCognitive/Functional Effects / Metastatic Cancers / Neurologic toxicity / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedNot AvailableAlzheimer's Disease (AD)1
3CompletedTreatmentAlzheimer's Disease (AD)4
3CompletedTreatmentAnxiety Disorders / Obsessive Compulsive Disorder (OCD)1
3CompletedTreatmentAutism Spectrum Conditions/Disorders1
3CompletedTreatmentDementia of the Alzheimer's Type1
3CompletedTreatmentDepression1
3CompletedTreatmentDisseminated Sclerosis1
3CompletedTreatmentFrontotemporal Dementia1
3CompletedTreatmentGeneral Anxiety Disorder, Social Anxiety Disorder1
3CompletedTreatmentHeadache, Tension-Type1
3CompletedTreatmentOpen-angle Glaucoma (OAG)2
3CompletedTreatmentSubstance Abuse1
3Enrolling by InvitationTreatmentAOD Effects and Consequences1
3Enrolling by InvitationTreatmentBipolar Disorder II1
3Not Yet RecruitingTreatmentAutism Spectrum Conditions/Disorders / Autism, Early Infantile / Nonverbal Learning Disability1
3Not Yet RecruitingTreatmentExcitotoxicity / Memantine / Stroke, Ischemic1
3RecruitingTreatmentMetastatic Brain Tumors1
3RecruitingTreatmentSchizophrenic Disorders1
3TerminatedPreventionSchizophrenic Disorders1
3TerminatedTreatmentAlzheimer's Disease (AD)2
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentChronic Schizophrenia1
3Unknown StatusTreatmentFibromyalgia1
4Active Not RecruitingTreatmentDepression / MCI1
4CompletedNot AvailableAlzheimer's Disease (AD)1
4CompletedBasic ScienceAlzheimer's Disease (AD)1
4CompletedTreatmentAlcohol Dependence / Depression1
4CompletedTreatmentAlzheimer Dementia (AD)1
4CompletedTreatmentAlzheimer's Disease (AD)11
4CompletedTreatmentAphasia / Strokes1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD)1
4CompletedTreatmentAutism Spectrum Conditions/Disorders1
4CompletedTreatmentBinge Eating Disorder (BED)1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentCRP1
4CompletedTreatmentDementia, Alzheimer Type1
4CompletedTreatmentDementias1
4CompletedTreatmentDepression1
4CompletedTreatmentDepression, Bipolar1
4CompletedTreatmentDepressive Disorders1
4CompletedTreatmentDiffuse Lewy Body Disease / Parkinson's Disease Dementia (PDD)1
4CompletedTreatmentDisseminated Sclerosis1
4CompletedTreatmentDown Syndrome (DS)1
4CompletedTreatmentFrontal Lobe Dementia / Frontotemporal Lobe Dementia / Semantic Dementia1
4CompletedTreatmentFrontotemporal Lobar Degeneration1
4CompletedTreatmentGait Disorders, Neurologic / Parkinson's Disease (PD)1
4CompletedTreatmentOculopalatal Tremor / Pendular Nystagmus1
4CompletedTreatmentOrganic Memory Impairment1
4CompletedTreatmentParkinson's Disease (PD)1
4CompletedTreatmentPhysiological Effects of Drugs1
4CompletedTreatmentPost Traumatic Stress Disorder (PTSD)1
4CompletedTreatmentSchizophrenic Disorders1
4CompletedTreatmentTremor, Essential1
4Not Yet RecruitingTreatmentAlzheimer's Disease (AD)1
4TerminatedPreventionDelirium / Post-Operative States1
4TerminatedTreatmentAlzheimer's Disease (AD)1
4TerminatedTreatmentMemory Disturbances / Mood1
4TerminatedTreatmentPain NOS1
4TerminatedTreatmentTraumatic Brain Injury (TBI)1
4Unknown StatusTreatmentAlzheimer's Disease (AD) / Dementias1
4Unknown StatusTreatmentAphasia / Strokes1
4Unknown StatusTreatmentDementias1
4Unknown StatusTreatmentHuntington's Disease (HD)1
4Unknown StatusTreatmentModerate to Severe Alzheimer's Disease1
4Unknown StatusTreatmentPost-Operative Pain1
Not AvailableCompletedBasic ScienceHealthy Individuals1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Executive Function Deficits (EFD)1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentBody Dysmorphic Disorders / Bulimia Nervosa (BN)1
Not AvailableCompletedTreatmentCognitive Impairments / Dementias / Parkinson's Disease (PD)1
Not AvailableCompletedTreatmentDementias1
Not AvailableCompletedTreatmentEpilepsies1
Not AvailableCompletedTreatmentNystagmus / Nystagmus, Pathological1
Not AvailableCompletedTreatmentObsessive Compulsive Disorder (OCD)1
Not AvailableCompletedTreatmentParkinson's Disease (PD)1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentTraumatic Brain Injury (TBI)1
Not AvailableRecruitingNot AvailableSchizophrenic Disorders1
Not AvailableUnknown StatusBasic ScienceSpinal Cord Injury, Chronic1
Not AvailableUnknown StatusPreventionMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentAlzheimer's Disease (AD)1
Not AvailableUnknown StatusTreatmentAsperger's Disorder / Autism, Early Infantile / Pervasive Developmental Disorder NOS1
Not AvailableUnknown StatusTreatmentDementias / Down Syndrome (DS) / Learning Disabilities1
Not AvailableUnknown StatusTreatmentFragile X Premutation Carriers / Fragile X-Associated Tremor/Ataxia Syndrome1
Not AvailableWithdrawnSupportive CareEpilepsies1
Not AvailableWithdrawnTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Executive Function Deficits (EFD's)1
Not AvailableWithdrawnTreatmentMajor Depressive Disorder (MDD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Bryant Ranch Prepack
  • Cardinal Health
  • Coupler Enterprises Inc.
  • Forest Laboratories Inc.
  • Forest Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Lundbeck Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Stat Rx Usa
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
TabletOral5 mg
Tablet, film coatedOral10 mg
Tablet, film coatedOral20 mg
SolutionOral5 mg/Pump actuation
TabletOral10 mg
Capsule, extended releaseOral
Capsule, extended releaseOral21 mg/1
Kit
LiquidOral2 mg/1mL
SolutionOral2 mg/1mL
Tablet, coatedOral10 mg/1
Tablet, coatedOral5 mg/1
SolutionOral5 mg / pump actuation
Tablet, film coatedOral10 mg/1
Tablet, film coatedOral5 mg/1
TabletOral10 mg/1
TabletOral5 mg/1
Capsule, extended releaseOral14 mg/1
Capsule, extended releaseOral28 mg/1
Capsule, extended releaseOral7 mg/1
CapsuleOral
KitOral
TabletOral5.0 mg
Prices
Unit descriptionCostUnit
Namenda 10 mg tablet3.38USD tablet
Namenda 5 mg tablet3.32USD tablet
Namenda 5-10 mg titration pk3.32USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2426492No2006-10-032023-05-08Canada
US8173708Yes2012-05-082026-05-22Us
US8283379Yes2012-10-092026-05-22Us
US8362085Yes2013-01-292026-05-22Us
US8039009Yes2011-10-182029-09-24Us
US8329752Yes2012-12-112026-05-22Us
US8598233Yes2013-12-032026-05-22Us
US8168209Yes2012-05-012026-05-22Us
US8338486No2012-12-252025-11-22Us
US8058291No2011-11-152029-12-05Us
US8580858No2013-11-122025-11-22Us
US8338485No2012-12-252025-11-22Us
US8293794No2012-10-232025-11-22Us
US5061703Yes1991-10-292015-10-11Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)258 °CPhysProp
water solubility35 mg/mL (HCl salt), 0.9 mg/mL for free baseNot Available
logP3.28HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0455 mg/mLALOGPS
logP3.31ALOGPS
logP2.07ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)10.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.49 m3·mol-1ChemAxon
Polarizability21.82 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9939
Blood Brain Barrier+0.9823
Caco-2 permeable+0.6082
P-glycoprotein substrateNon-substrate0.6403
P-glycoprotein inhibitor INon-inhibitor0.82
P-glycoprotein inhibitor IINon-inhibitor0.7555
Renal organic cation transporterNon-inhibitor0.7774
CYP450 2C9 substrateNon-substrate0.8213
CYP450 2D6 substrateNon-substrate0.6153
CYP450 3A4 substrateNon-substrate0.5319
CYP450 1A2 substrateNon-inhibitor0.9327
CYP450 2C9 inhibitorNon-inhibitor0.9281
CYP450 2D6 inhibitorNon-inhibitor0.872
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6795
Ames testNon AMES toxic0.6945
CarcinogenicityNon-carcinogens0.7426
BiodegradationNot ready biodegradable0.9633
Rat acute toxicity2.3455 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9839
hERG inhibition (predictor II)Non-inhibitor0.6818
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03e9-0900000000-65172d14e0f6b9102d73
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-ce475f103d528ff4d342
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-1c9199c5cf1c902223ae
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-08fr-0900000000-1bac817f714e7eec7488
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-2900000000-eb58e236084a93a3d37b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-4900000000-5a87d54400c3e9720ad0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-9500000000-95eb2b63a2392449ec4a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9100000000-608b372857aacd60eb61
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00kf-9000000000-f283a81168372575c2aa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-bbf1127413d0f995a000

Taxonomy

Description
This compound belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing an primary aliphatic amine group.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Monoalkylamines
Alternative Parents
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Organopnictogen compound / Hydrocarbon derivative / Primary aliphatic amine / Aliphatic homopolycyclic compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
adamantanes, primary aliphatic amine (CHEBI:64312)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein phosphatase 2a binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May ...
Gene Name
GRIN3A
Uniprot ID
Q8TCU5
Uniprot Name
Glutamate receptor ionotropic, NMDA 3A
Molecular Weight
125464.07 Da
References
  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. [PubMed:17502428]
  2. Chatterton JE, Awobuluyi M, Premkumar LS, Takahashi H, Talantova M, Shin Y, Cui J, Tu S, Sevarino KA, Nakanishi N, Tong G, Lipton SA, Zhang D: Excitatory glycine receptors containing the NR3 family of NMDA receptor subunits. Nature. 2002 Feb 14;415(6873):793-8. Epub 2002 Jan 30. [PubMed:11823786]
  3. Schrattenholz A, Soskic V: NMDA receptors are not alone: dynamic regulation of NMDA receptor structure and function by neuregulins and transient cholesterol-rich membrane domains leads to disease-specific nuances of glutamate-signalling. Curr Top Med Chem. 2006;6(7):663-86. [PubMed:16719808]
  4. Foster AC, Kemp JA: Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17. Epub 2005 Dec 22. [PubMed:16377242]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of sub...
Gene Name
GRIN2A
Uniprot ID
Q12879
Uniprot Name
Glutamate receptor ionotropic, NMDA 2A
Molecular Weight
165281.215 Da
References
  1. Chen HS, Lipton SA: Pharmacological implications of two distinct mechanisms of interaction of memantine with N-methyl-D-aspartate-gated channels. J Pharmacol Exp Ther. 2005 Sep;314(3):961-71. Epub 2005 May 18. [PubMed:15901795]
  2. Maler JM, Esselmann H, Wiltfang J, Kunz N, Lewczuk P, Reulbach U, Bleich S, Ruther E, Kornhuber J: Memantine inhibits ethanol-induced NMDA receptor up-regulation in rat hippocampal neurons. Brain Res. 2005 Aug 9;1052(2):156-62. [PubMed:16009352]
  3. Bresink I, Benke TA, Collett VJ, Seal AJ, Parsons CG, Henley JM, Collingridge GL: Effects of memantine on recombinant rat NMDA receptors expressed in HEK 293 cells. Br J Pharmacol. 1996 Sep;119(2):195-204. [PubMed:8886398]
  4. Blanpied TA, Boeckman FA, Aizenman E, Johnson JW: Trapping channel block of NMDA-activated responses by amantadine and memantine. J Neurophysiol. 1997 Jan;77(1):309-23. [PubMed:9120573]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
Gene Name
GRIN2B
Uniprot ID
Q13224
Uniprot Name
Glutamate receptor ionotropic, NMDA 2B
Molecular Weight
166365.885 Da
References
  1. Kashiwagi K, Masuko T, Nguyen CD, Kuno T, Tanaka I, Igarashi K, Williams K: Channel blockers acting at N-methyl-D-aspartate receptors: differential effects of mutations in the vestibule and ion channel pore. Mol Pharmacol. 2002 Mar;61(3):533-45. [PubMed:11854433]
  2. Nakazato E, Kato A, Watanabe S: Brain but not spinal NR2B receptor is responsible for the anti-allodynic effect of an NR2B subunit-selective antagonist CP-101,606 in a rat chronic constriction injury model. Pharmacology. 2005 Jan;73(1):8-14. Epub 2004 Sep 27. [PubMed:15452358]
  3. Maler JM, Esselmann H, Wiltfang J, Kunz N, Lewczuk P, Reulbach U, Bleich S, Ruther E, Kornhuber J: Memantine inhibits ethanol-induced NMDA receptor up-regulation in rat hippocampal neurons. Brain Res. 2005 Aug 9;1052(2):156-62. [PubMed:16009352]
  4. Blanpied TA, Boeckman FA, Aizenman E, Johnson JW: Trapping channel block of NMDA-activated responses by amantadine and memantine. J Neurophysiol. 1997 Jan;77(1):309-23. [PubMed:9120573]
  5. Rogawski MA, Wenk GL: The neuropharmacological basis for the use of memantine in the treatment of Alzheimer's disease. CNS Drug Rev. 2003 Fall;9(3):275-308. [PubMed:14530799]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated potassium channel activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name
HTR3A
Uniprot ID
P46098
Uniprot Name
5-hydroxytryptamine receptor 3A
Molecular Weight
55279.835 Da
References
  1. Rammes G, Rupprecht R, Ferrari U, Zieglgansberger W, Parsons CG: The N-methyl-D-aspartate receptor channel blockers memantine, MRZ 2/579 and other amino-alkyl-cyclohexanes antagonise 5-HT(3) receptor currents in cultured HEK-293 and N1E-115 cell systems in a non-competitive manner. Neurosci Lett. 2001 Jun 22;306(1-2):81-4. [PubMed:11403963]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Not Available
Specific Function
Not Available
Gene Name
CHRNA7
Uniprot ID
Q693P7
Uniprot Name
Alpha-7 nicotinic cholinergic receptor subunit
Molecular Weight
2987.635 Da
References
  1. Aracava Y, Pereira EF, Maelicke A, Albuquerque EX: Memantine blocks alpha7* nicotinic acetylcholine receptors more potently than n-methyl-D-aspartate receptors in rat hippocampal neurons. J Pharmacol Exp Ther. 2005 Mar;312(3):1195-205. Epub 2004 Nov 2. [PubMed:15522999]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Potassium channel regulator activity
Specific Function
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
DRD2
Uniprot ID
P14416
Uniprot Name
D(2) dopamine receptor
Molecular Weight
50618.91 Da
References
  1. Seeman P, Caruso C, Lasaga M: Memantine agonist action at dopamine D2High receptors. Synapse. 2008 Feb;62(2):149-53. [PubMed:18000814]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 Da
References
  1. Kotermanski SE, Wood JT, Johnson JW: Memantine binding to a superficial site on NMDA receptors contributes to partial trapping. J Physiol. 2009 Oct 1;587(Pt 19):4589-604. doi: 10.1113/jphysiol.2009.176297. Epub 2009 Aug 17. [PubMed:19687120]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Micuda S, Mundlova L, Anzenbacherova E, Anzenbacher P, Chladek J, Fuksa L, Martinkova J: Inhibitory effects of memantine on human cytochrome P450 activities: prediction of in vivo drug interactions. Eur J Clin Pharmacol. 2004 Oct;60(8):583-9. doi: 10.1007/s00228-004-0825-1. Epub 2004 Sep 16. [PubMed:15378224]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
There is limited current data available on this enzyme inhibition, with the exception of one in vitro study.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Micuda S, Mundlova L, Anzenbacherova E, Anzenbacher P, Chladek J, Fuksa L, Martinkova J: Inhibitory effects of memantine on human cytochrome P450 activities: prediction of in vivo drug interactions. Eur J Clin Pharmacol. 2004 Oct;60(8):583-9. doi: 10.1007/s00228-004-0825-1. Epub 2004 Sep 16. [PubMed:15378224]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 05:32